JPS6121631B2 - - Google Patents
Info
- Publication number
- JPS6121631B2 JPS6121631B2 JP57209466A JP20946682A JPS6121631B2 JP S6121631 B2 JPS6121631 B2 JP S6121631B2 JP 57209466 A JP57209466 A JP 57209466A JP 20946682 A JP20946682 A JP 20946682A JP S6121631 B2 JPS6121631 B2 JP S6121631B2
- Authority
- JP
- Japan
- Prior art keywords
- penten
- methyl
- triazol
- methoxy
- ethoxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 claims description 100
- 239000000203 mixture Substances 0.000 claims description 16
- 230000000855 fungicidal effect Effects 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 9
- 230000012010 growth Effects 0.000 claims description 8
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 7
- 230000003115 biocidal effect Effects 0.000 claims description 7
- 239000003139 biocide Substances 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 claims description 6
- IMGLRFNWBUPBMG-UHFFFAOYSA-N 2-pent-1-enyl-1h-pyrrole Chemical class CCCC=CC1=CC=CN1 IMGLRFNWBUPBMG-UHFFFAOYSA-N 0.000 claims description 6
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 230000002363 herbicidal effect Effects 0.000 claims description 4
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- 235000005985 organic acids Nutrition 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 230000001105 regulatory effect Effects 0.000 claims description 3
- GBVRBUQIYZAPRA-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-4-methoxy-4-methyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-one Chemical class C1=NC=NN1C(C(=O)C(C)(C)OC)=CC1=CC=C(Cl)C=C1Cl GBVRBUQIYZAPRA-UHFFFAOYSA-N 0.000 claims description 2
- AFYNJULFXCZJQX-UHFFFAOYSA-N 1-(2,6-dichlorophenyl)-4-methoxy-4-methyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-one Chemical class C1=NC=NN1C(C(=O)C(C)(C)OC)=CC1=C(Cl)C=CC=C1Cl AFYNJULFXCZJQX-UHFFFAOYSA-N 0.000 claims description 2
- GWLGUWJMWOTFES-UHFFFAOYSA-N 1-(2-chlorophenyl)-4-methoxy-4-methyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol Chemical compound C1=NC=NN1C(C(O)C(C)(C)OC)=CC1=CC=CC=C1Cl GWLGUWJMWOTFES-UHFFFAOYSA-N 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- VHVMXWZXFBOANQ-UHFFFAOYSA-N 1-Penten-3-ol Chemical compound CCC(O)C=C VHVMXWZXFBOANQ-UHFFFAOYSA-N 0.000 claims 8
- JLIDVCMBCGBIEY-UHFFFAOYSA-N 1-penten-3-one Chemical compound CCC(=O)C=C JLIDVCMBCGBIEY-UHFFFAOYSA-N 0.000 claims 6
- ZEQWGGDIFYDUIT-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-4-methoxy-4-methyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-one Chemical compound C1=NC=NN1C(C(=O)C(C)(C)OC)=CC1=CC=C(Cl)C(Cl)=C1 ZEQWGGDIFYDUIT-UHFFFAOYSA-N 0.000 claims 2
- QJAOJJYGUNXTOD-UHFFFAOYSA-N 4-ethoxy-1-(4-methoxyphenyl)-4-methyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-one Chemical class C1=NC=NN1C(C(=O)C(C)(C)OCC)=CC1=CC=C(OC)C=C1 QJAOJJYGUNXTOD-UHFFFAOYSA-N 0.000 claims 2
- XYRANCVKHSZBPM-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-4-ethoxy-4-methyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol Chemical class C1=NC=NN1C(C(O)C(C)(C)OCC)=CC1=CC=C(Cl)C=C1Cl XYRANCVKHSZBPM-UHFFFAOYSA-N 0.000 claims 1
- ZVOVLUCBCRZRRY-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-4-ethoxy-4-methyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-one Chemical class C1=NC=NN1C(C(=O)C(C)(C)OCC)=CC1=CC=C(Cl)C=C1Cl ZVOVLUCBCRZRRY-UHFFFAOYSA-N 0.000 claims 1
- RREUISKGZAOKFS-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-4-methoxy-4-methyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol Chemical class C1=NC=NN1C(C(O)C(C)(C)OC)=CC1=CC=C(Cl)C=C1Cl RREUISKGZAOKFS-UHFFFAOYSA-N 0.000 claims 1
- AUSDAWNMIXUGPI-UHFFFAOYSA-N 1-(2,6-dichlorophenyl)-4-methoxy-4-methyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol Chemical class C1=NC=NN1C(C(O)C(C)(C)OC)=CC1=C(Cl)C=CC=C1Cl AUSDAWNMIXUGPI-UHFFFAOYSA-N 0.000 claims 1
- HOALVMLRJANHMI-UHFFFAOYSA-N 1-(2-chlorophenyl)-4-ethoxy-4-methyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol Chemical compound C1=NC=NN1C(C(O)C(C)(C)OCC)=CC1=CC=CC=C1Cl HOALVMLRJANHMI-UHFFFAOYSA-N 0.000 claims 1
- SLFFZYKCUSQQQD-UHFFFAOYSA-N 1-(2-chlorophenyl)-4-ethoxy-4-methyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-one Chemical compound C1=NC=NN1C(C(=O)C(C)(C)OCC)=CC1=CC=CC=C1Cl SLFFZYKCUSQQQD-UHFFFAOYSA-N 0.000 claims 1
- MVOTUXRZDSLOEP-UHFFFAOYSA-N 1-(2-fluorophenyl)-4-methoxy-4-methyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-one Chemical class C1=NC=NN1C(C(=O)C(C)(C)OC)=CC1=CC=CC=C1F MVOTUXRZDSLOEP-UHFFFAOYSA-N 0.000 claims 1
- DUOJLBFTLFQBEQ-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-4-ethoxy-4-methyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol Chemical class C1=NC=NN1C(C(O)C(C)(C)OCC)=CC1=CC=C(Cl)C(Cl)=C1 DUOJLBFTLFQBEQ-UHFFFAOYSA-N 0.000 claims 1
- HIOGFWNCJFIZHM-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-4-ethoxy-4-methyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-one Chemical class C1=NC=NN1C(C(=O)C(C)(C)OCC)=CC1=CC=C(Cl)C(Cl)=C1 HIOGFWNCJFIZHM-UHFFFAOYSA-N 0.000 claims 1
- FMEPSSFQQBVGTO-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-4-methoxy-4-methyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol Chemical class C1=NC=NN1C(C(O)C(C)(C)OC)=CC1=CC=C(Cl)C(Cl)=C1 FMEPSSFQQBVGTO-UHFFFAOYSA-N 0.000 claims 1
- TTWZKOUBINPWEP-UHFFFAOYSA-N 1-(3-chlorophenyl)-4-methoxy-4-methyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol Chemical compound C1=NC=NN1C(C(O)C(C)(C)OC)=CC1=CC=CC(Cl)=C1 TTWZKOUBINPWEP-UHFFFAOYSA-N 0.000 claims 1
- SOFXASRMHYCZQS-UHFFFAOYSA-N 1-(3-chlorophenyl)-4-methoxy-4-methyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-one Chemical compound C1=NC=NN1C(C(=O)C(C)(C)OC)=CC1=CC=CC(Cl)=C1 SOFXASRMHYCZQS-UHFFFAOYSA-N 0.000 claims 1
- LREOVOMGVWNBHI-UHFFFAOYSA-N 1-(4-bromophenyl)-4-ethoxy-4-methyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol Chemical compound C1=NC=NN1C(C(O)C(C)(C)OCC)=CC1=CC=C(Br)C=C1 LREOVOMGVWNBHI-UHFFFAOYSA-N 0.000 claims 1
- VCORWRMAHYTBCT-UHFFFAOYSA-N 1-(4-bromophenyl)-4-ethoxy-4-methyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-one Chemical compound C1=NC=NN1C(C(=O)C(C)(C)OCC)=CC1=CC=C(Br)C=C1 VCORWRMAHYTBCT-UHFFFAOYSA-N 0.000 claims 1
- KOTSYFPDBSURJD-UHFFFAOYSA-N 1-(4-bromophenyl)-4-methoxy-4-methyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol Chemical compound C1=NC=NN1C(C(O)C(C)(C)OC)=CC1=CC=C(Br)C=C1 KOTSYFPDBSURJD-UHFFFAOYSA-N 0.000 claims 1
- DYAQUNUDMWSBPX-UHFFFAOYSA-N 1-(4-bromophenyl)-4-methoxy-4-methyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-one Chemical compound C1=NC=NN1C(C(=O)C(C)(C)OC)=CC1=CC=C(Br)C=C1 DYAQUNUDMWSBPX-UHFFFAOYSA-N 0.000 claims 1
- SVHMKVUIKNAFAA-UHFFFAOYSA-N 1-(4-chlorophenyl)-4-ethoxy-4-methyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol Chemical compound C1=NC=NN1C(C(O)C(C)(C)OCC)=CC1=CC=C(Cl)C=C1 SVHMKVUIKNAFAA-UHFFFAOYSA-N 0.000 claims 1
- JMMDOTLVESRDOC-UHFFFAOYSA-N 1-(4-chlorophenyl)-4-methoxy-4-methyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol Chemical compound C1=NC=NN1C(C(O)C(C)(C)OC)=CC1=CC=C(Cl)C=C1 JMMDOTLVESRDOC-UHFFFAOYSA-N 0.000 claims 1
- RBHGCSNPQZOEOL-UHFFFAOYSA-N 1-(4-fluorophenyl)-4-methoxy-4-methyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol Chemical class C1=NC=NN1C(C(O)C(C)(C)OC)=CC1=CC=C(F)C=C1 RBHGCSNPQZOEOL-UHFFFAOYSA-N 0.000 claims 1
- OLEXHJCNFTYOJU-UHFFFAOYSA-N 1-(4-fluorophenyl)-4-methoxy-4-methyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-one Chemical class C1=NC=NN1C(C(=O)C(C)(C)OC)=CC1=CC=C(F)C=C1 OLEXHJCNFTYOJU-UHFFFAOYSA-N 0.000 claims 1
- IYSULHDVNHHGTI-UHFFFAOYSA-N 2-imidazol-1-yl-4-methoxy-4-methyl-1-thiophen-2-ylpent-1-en-3-one Chemical compound C1=CN=CN1C(C(=O)C(C)(C)OC)=CC1=CC=CS1 IYSULHDVNHHGTI-UHFFFAOYSA-N 0.000 claims 1
- AWCPFDZNCWOVHZ-UHFFFAOYSA-N 4-butoxy-1-(2-chlorophenyl)-4-methyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol Chemical class C1=NC=NN1C(C(O)C(C)(C)OCCCC)=CC1=CC=CC=C1Cl AWCPFDZNCWOVHZ-UHFFFAOYSA-N 0.000 claims 1
- XWRNHLZDWQGHLT-UHFFFAOYSA-N 4-butoxy-1-(2-chlorophenyl)-4-methyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-one Chemical compound C1=NC=NN1C(C(=O)C(C)(C)OCCCC)=CC1=CC=CC=C1Cl XWRNHLZDWQGHLT-UHFFFAOYSA-N 0.000 claims 1
- LIUJZJDSJLTAEO-UHFFFAOYSA-N 4-butoxy-1-(4-chlorophenyl)-4-methyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol Chemical class C1=NC=NN1C(C(O)C(C)(C)OCCCC)=CC1=CC=C(Cl)C=C1 LIUJZJDSJLTAEO-UHFFFAOYSA-N 0.000 claims 1
- GYYQCPJCFMSWLF-UHFFFAOYSA-N 4-butoxy-1-(4-chlorophenyl)-4-methyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-one Chemical compound C1=NC=NN1C(C(=O)C(C)(C)OCCCC)=CC1=CC=C(Cl)C=C1 GYYQCPJCFMSWLF-UHFFFAOYSA-N 0.000 claims 1
- XXVMHDMIYIIOMI-UHFFFAOYSA-N 4-ethoxy-1-(2-fluorophenyl)-4-methyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol Chemical class C1=NC=NN1C(C(O)C(C)(C)OCC)=CC1=CC=CC=C1F XXVMHDMIYIIOMI-UHFFFAOYSA-N 0.000 claims 1
- GQAITMYBNRERAK-UHFFFAOYSA-N 4-ethoxy-1-(2-fluorophenyl)-4-methyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-one Chemical class C1=NC=NN1C(C(=O)C(C)(C)OCC)=CC1=CC=CC=C1F GQAITMYBNRERAK-UHFFFAOYSA-N 0.000 claims 1
- RFDJSHVRSHPDRL-UHFFFAOYSA-N 4-ethoxy-1-(4-fluorophenyl)-4-methyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol Chemical class C1=NC=NN1C(C(O)C(C)(C)OCC)=CC1=CC=C(F)C=C1 RFDJSHVRSHPDRL-UHFFFAOYSA-N 0.000 claims 1
- UGZPYDRJDYWFMH-UHFFFAOYSA-N 4-ethoxy-1-(furan-2-yl)-4-methyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol Chemical compound C1=NC=NN1C(C(O)C(C)(C)OCC)=CC1=CC=CO1 UGZPYDRJDYWFMH-UHFFFAOYSA-N 0.000 claims 1
- BMZYNQULFKBORI-UHFFFAOYSA-N 4-ethoxy-1-(furan-2-yl)-4-methyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-one Chemical compound C1=NC=NN1C(C(=O)C(C)(C)OCC)=CC1=CC=CO1 BMZYNQULFKBORI-UHFFFAOYSA-N 0.000 claims 1
- CXCZRCJTXZJQKU-UHFFFAOYSA-N 4-ethoxy-4-methyl-1-(2-methylphenyl)-2-(1,2,4-triazol-1-yl)pent-1-en-3-one Chemical compound C1=NC=NN1C(C(=O)C(C)(C)OCC)=CC1=CC=CC=C1C CXCZRCJTXZJQKU-UHFFFAOYSA-N 0.000 claims 1
- ZIEXJVYJHVCUOJ-UHFFFAOYSA-N 4-ethoxy-4-methyl-1-(4-methylphenyl)-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol Chemical compound C1=NC=NN1C(C(O)C(C)(C)OCC)=CC1=CC=C(C)C=C1 ZIEXJVYJHVCUOJ-UHFFFAOYSA-N 0.000 claims 1
- WZADGLBFUIKDKI-UHFFFAOYSA-N 4-ethoxy-4-methyl-1-(4-methylphenyl)-2-(1,2,4-triazol-1-yl)pent-1-en-3-one Chemical compound C1=NC=NN1C(C(=O)C(C)(C)OCC)=CC1=CC=C(C)C=C1 WZADGLBFUIKDKI-UHFFFAOYSA-N 0.000 claims 1
- WDCHBTKJYMFAJS-UHFFFAOYSA-N 4-ethoxy-4-methyl-1-(4-nitrophenyl)-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol Chemical compound C1=NC=NN1C(C(O)C(C)(C)OCC)=CC1=CC=C([N+]([O-])=O)C=C1 WDCHBTKJYMFAJS-UHFFFAOYSA-N 0.000 claims 1
- SPZNUKPUJBVEFW-UHFFFAOYSA-N 4-ethoxy-4-methyl-1-(4-nitrophenyl)-2-(1,2,4-triazol-1-yl)pent-1-en-3-one Chemical compound C1=NC=NN1C(C(=O)C(C)(C)OCC)=CC1=CC=C([N+]([O-])=O)C=C1 SPZNUKPUJBVEFW-UHFFFAOYSA-N 0.000 claims 1
- ROUPIUBHFJLRMU-UHFFFAOYSA-N 4-ethoxy-4-methyl-1-naphthalen-2-yl-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol Chemical compound C=1C=C2C=CC=CC2=CC=1C=C(C(O)C(C)(C)OCC)N1C=NC=N1 ROUPIUBHFJLRMU-UHFFFAOYSA-N 0.000 claims 1
- ABIYUWJNHDSLTF-UHFFFAOYSA-N 4-ethoxy-4-methyl-1-naphthalen-2-yl-2-(1,2,4-triazol-1-yl)pent-1-en-3-one Chemical compound C=1C=C2C=CC=CC2=CC=1C=C(C(=O)C(C)(C)OCC)N1C=NC=N1 ABIYUWJNHDSLTF-UHFFFAOYSA-N 0.000 claims 1
- PMTVSMLQVYOANZ-UHFFFAOYSA-N 4-ethoxy-4-methyl-1-phenyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol Chemical compound C1=NC=NN1C(C(O)C(C)(C)OCC)=CC1=CC=CC=C1 PMTVSMLQVYOANZ-UHFFFAOYSA-N 0.000 claims 1
- BLVCXLJHLFYFCJ-UHFFFAOYSA-N 4-ethoxy-4-methyl-1-pyridin-3-yl-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol Chemical compound C1=NC=NN1C(C(O)C(C)(C)OCC)=CC1=CC=CN=C1 BLVCXLJHLFYFCJ-UHFFFAOYSA-N 0.000 claims 1
- NYUAQBBEITUIBV-UHFFFAOYSA-N 4-ethoxy-4-methyl-1-pyridin-3-yl-2-(1,2,4-triazol-1-yl)pent-1-en-3-one Chemical compound C1=NC=NN1C(C(=O)C(C)(C)OCC)=CC1=CC=CN=C1 NYUAQBBEITUIBV-UHFFFAOYSA-N 0.000 claims 1
- JGYOUFROHBQDSL-UHFFFAOYSA-N 4-ethoxy-4-methyl-1-thiophen-2-yl-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol Chemical compound C1=NC=NN1C(C(O)C(C)(C)OCC)=CC1=CC=CS1 JGYOUFROHBQDSL-UHFFFAOYSA-N 0.000 claims 1
- PWSRGIWNSVFDCN-UHFFFAOYSA-N 4-ethoxy-4-methyl-1-thiophen-2-yl-2-(1,2,4-triazol-1-yl)pent-1-en-3-one Chemical compound C1=NC=NN1C(C(=O)C(C)(C)OCC)=CC1=CC=CS1 PWSRGIWNSVFDCN-UHFFFAOYSA-N 0.000 claims 1
- VEDUNQXOXKZOSN-UHFFFAOYSA-N 4-methoxy-1-(4-methoxyphenyl)-4-methyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol Chemical class C1=CC(OC)=CC=C1C=C(C(O)C(C)(C)OC)N1N=CN=C1 VEDUNQXOXKZOSN-UHFFFAOYSA-N 0.000 claims 1
- NMHQXBWSLWEKBB-UHFFFAOYSA-N 4-methoxy-1-(4-methoxyphenyl)-4-methyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-one Chemical class C1=CC(OC)=CC=C1C=C(C(=O)C(C)(C)OC)N1N=CN=C1 NMHQXBWSLWEKBB-UHFFFAOYSA-N 0.000 claims 1
- MUEHVKSIFUEEME-UHFFFAOYSA-N 4-methoxy-4-methyl-1-(2-methylphenyl)-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol Chemical compound C1=NC=NN1C(C(O)C(C)(C)OC)=CC1=CC=CC=C1C MUEHVKSIFUEEME-UHFFFAOYSA-N 0.000 claims 1
- BEFMPPNCGLCJHC-UHFFFAOYSA-N 4-methoxy-4-methyl-1-(2-methylphenyl)-2-(1,2,4-triazol-1-yl)pent-1-en-3-one Chemical compound C1=NC=NN1C(C(=O)C(C)(C)OC)=CC1=CC=CC=C1C BEFMPPNCGLCJHC-UHFFFAOYSA-N 0.000 claims 1
- OAGNWYBHOZRWPI-UHFFFAOYSA-N 4-methoxy-4-methyl-1-(4-methylphenyl)-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol Chemical compound C1=NC=NN1C(C(O)C(C)(C)OC)=CC1=CC=C(C)C=C1 OAGNWYBHOZRWPI-UHFFFAOYSA-N 0.000 claims 1
- IXBUJBJDJYQFHX-UHFFFAOYSA-N 4-methoxy-4-methyl-1-(4-methylphenyl)-2-(1,2,4-triazol-1-yl)pent-1-en-3-one Chemical compound C1=NC=NN1C(C(=O)C(C)(C)OC)=CC1=CC=C(C)C=C1 IXBUJBJDJYQFHX-UHFFFAOYSA-N 0.000 claims 1
- OKMZGDGNJUNQIH-UHFFFAOYSA-N 4-methoxy-4-methyl-1-(4-nitrophenyl)-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol Chemical compound C1=NC=NN1C(C(O)C(C)(C)OC)=CC1=CC=C([N+]([O-])=O)C=C1 OKMZGDGNJUNQIH-UHFFFAOYSA-N 0.000 claims 1
- WAHUBXLGCPZKQW-UHFFFAOYSA-N 4-methoxy-4-methyl-1-(4-nitrophenyl)-2-(1,2,4-triazol-1-yl)pent-1-en-3-one Chemical compound C1=NC=NN1C(C(=O)C(C)(C)OC)=CC1=CC=C([N+]([O-])=O)C=C1 WAHUBXLGCPZKQW-UHFFFAOYSA-N 0.000 claims 1
- HZFSIDIODOEBQD-UHFFFAOYSA-N 4-methoxy-4-methyl-1-phenyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol Chemical compound C1=NC=NN1C(C(O)C(C)(C)OC)=CC1=CC=CC=C1 HZFSIDIODOEBQD-UHFFFAOYSA-N 0.000 claims 1
- QQWXOKIAWXUXFL-UHFFFAOYSA-N 4-methoxy-4-methyl-1-pyridin-2-yl-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol Chemical compound C1=NC=NN1C(C(O)C(C)(C)OC)=CC1=CC=CC=N1 QQWXOKIAWXUXFL-UHFFFAOYSA-N 0.000 claims 1
- DISALJGBQQQNTB-UHFFFAOYSA-N 4-methoxy-4-methyl-1-thiophen-2-yl-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol Chemical compound C1=NC=NN1C(C(O)C(C)(C)OC)=CC1=CC=CS1 DISALJGBQQQNTB-UHFFFAOYSA-N 0.000 claims 1
- RXVSBOOYONUZLA-UHFFFAOYSA-N 4-methoxy-4-methyl-1-thiophen-2-yl-2-(1,2,4-triazol-1-yl)pent-1-en-3-one Chemical compound C1=NC=NN1C(C(=O)C(C)(C)OC)=CC1=CC=CS1 RXVSBOOYONUZLA-UHFFFAOYSA-N 0.000 claims 1
- XXMDRYHZUVZAOM-UHFFFAOYSA-N N1(C=NC=C1)C=CC(C(C)(C)OC)=O Chemical compound N1(C=NC=C1)C=CC(C(C)(C)OC)=O XXMDRYHZUVZAOM-UHFFFAOYSA-N 0.000 claims 1
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- 150000007513 acids Chemical class 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 150000008107 benzenesulfonic acids Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000000249 desinfective effect Effects 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 230000024346 drought recovery Effects 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 230000013020 embryo development Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 230000005089 fruit drop Effects 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000009422 growth inhibiting effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000002054 inoculum Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 230000002262 irrigation Effects 0.000 description 1
- 238000003973 irrigation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 230000005087 leaf formation Effects 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 244000000010 microbial pathogen Species 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 210000002741 palatine tonsil Anatomy 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229940044654 phenolsulfonic acid Drugs 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 230000005070 ripening Effects 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000429 sodium aluminium silicate Substances 0.000 description 1
- 235000012217 sodium aluminium silicate Nutrition 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 230000004763 spore germination Effects 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 244000045561 useful plants Species 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19813148742 DE3148742A1 (de) | 1981-12-04 | 1981-12-04 | Azolyl-penten-derivate, verfahren zur herstellung dieser verbindungen sowie diese enthaltende biozide mittel |
| DE3148742.4 | 1981-12-04 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58103368A JPS58103368A (ja) | 1983-06-20 |
| JPS6121631B2 true JPS6121631B2 (fi) | 1986-05-28 |
Family
ID=6148277
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57209466A Granted JPS58103368A (ja) | 1981-12-04 | 1982-12-01 | アゾリル−ペンテン誘導体、その製法および該誘導体を含有する殺生剤 |
Country Status (37)
| Country | Link |
|---|---|
| US (1) | US4517367A (fi) |
| JP (1) | JPS58103368A (fi) |
| KR (1) | KR880002041B1 (fi) |
| AR (1) | AR231835A1 (fi) |
| AT (1) | AT381837B (fi) |
| AU (1) | AU556935B2 (fi) |
| BE (1) | BE895213A (fi) |
| BG (1) | BG37072A3 (fi) |
| CA (1) | CA1194481A (fi) |
| CH (1) | CH651559A5 (fi) |
| CS (1) | CS230597B2 (fi) |
| DD (1) | DD208294A5 (fi) |
| DE (1) | DE3148742A1 (fi) |
| DK (1) | DK537982A (fi) |
| ES (1) | ES517288A0 (fi) |
| FI (1) | FI823910L (fi) |
| FR (1) | FR2517673B1 (fi) |
| GB (1) | GB2110687B (fi) |
| GR (1) | GR79557B (fi) |
| HU (1) | HU188821B (fi) |
| IL (1) | IL67403A (fi) |
| IT (1) | IT1156131B (fi) |
| LU (1) | LU84495A1 (fi) |
| MA (1) | MA19651A1 (fi) |
| NL (1) | NL8203818A (fi) |
| NO (1) | NO824071L (fi) |
| NZ (1) | NZ202569A (fi) |
| PH (1) | PH20418A (fi) |
| PL (1) | PL131542B1 (fi) |
| PT (1) | PT75856A (fi) |
| RO (1) | RO85812B (fi) |
| SE (1) | SE453829B (fi) |
| SU (1) | SU1179923A3 (fi) |
| TR (1) | TR21791A (fi) |
| YU (1) | YU217582A (fi) |
| ZA (1) | ZA828916B (fi) |
| ZW (1) | ZW25682A1 (fi) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1150706B (it) * | 1982-03-19 | 1986-12-17 | Montedison Spa | Derivati di eterociclici azotati dotati di attivita' fitoregolatrice |
| DE3229274A1 (de) * | 1982-08-05 | 1984-02-09 | Bayer Ag, 5090 Leverkusen | Substituierte azolylvinyl-ketone und -carbinole |
| DE3340989A1 (de) * | 1983-11-10 | 1985-05-23 | Schering AG, 1000 Berlin und 4709 Bergkamen | E-triazolyl-pentenole, verfahren zur herstellung dieser verbindungen sowie diese enthaltende biozide und wuchsregulatorische mittel |
| DE4334135A1 (de) * | 1993-10-07 | 1995-04-13 | Merck Patent Gmbh | Verfahren zur Herstellung von Pilocarpin-Derivaten |
| CN103965273B (zh) | 2013-08-23 | 2016-05-25 | 普莱柯生物工程股份有限公司 | 一种大环内酯类化合物 |
| US10743535B2 (en) | 2017-08-18 | 2020-08-18 | H&K Solutions Llc | Insecticide for flight-capable pests |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4554007A (en) * | 1979-03-20 | 1985-11-19 | Sumitomo Chemical Company, Limited | Geometrical isomer of 1-substituted-1-triazolylstyrenes, and their production and use as fungicide, herbicide and/or plant growth regulant |
| GB2075005A (en) * | 1980-05-01 | 1981-11-11 | Ici Ltd | Fungicidal Imidazole and Triazole Derivatives |
| GB2075004A (en) * | 1980-05-01 | 1981-11-11 | Ici Ltd | Fungicidal Imidazole and Triazole Derivatives |
| DE3026140A1 (de) * | 1980-07-10 | 1982-02-18 | Basf Ag, 6700 Ludwigshafen | 1,3-dioxan-5-yl-alkenyltriazole, ihre herstellung, ihre verwendung zur regulierung des pflanzenwachstums und mittel dafuer |
| DE3229274A1 (de) * | 1982-08-05 | 1984-02-09 | Bayer Ag, 5090 Leverkusen | Substituierte azolylvinyl-ketone und -carbinole |
-
1981
- 1981-12-04 DE DE19813148742 patent/DE3148742A1/de not_active Withdrawn
-
1982
- 1982-09-28 YU YU02175/82A patent/YU217582A/xx unknown
- 1982-09-30 NL NL8203818A patent/NL8203818A/nl not_active Application Discontinuation
- 1982-11-05 TR TR21791A patent/TR21791A/xx unknown
- 1982-11-11 ES ES517288A patent/ES517288A0/es active Granted
- 1982-11-15 PT PT75856A patent/PT75856A/pt unknown
- 1982-11-15 FI FI823910A patent/FI823910L/fi not_active Application Discontinuation
- 1982-11-18 AU AU90704/82A patent/AU556935B2/en not_active Expired - Fee Related
- 1982-11-22 NZ NZ202569A patent/NZ202569A/en unknown
- 1982-11-24 MA MA19864A patent/MA19651A1/fr unknown
- 1982-11-29 GB GB08233996A patent/GB2110687B/en not_active Expired
- 1982-11-30 SU SU823521075A patent/SU1179923A3/ru active
- 1982-12-01 LU LU84495A patent/LU84495A1/de unknown
- 1982-12-01 CH CH6994/82A patent/CH651559A5/de not_active IP Right Cessation
- 1982-12-01 JP JP57209466A patent/JPS58103368A/ja active Granted
- 1982-12-01 BE BE0/209622A patent/BE895213A/fr not_active IP Right Cessation
- 1982-12-01 AR AR291458A patent/AR231835A1/es active
- 1982-12-02 AT AT0438682A patent/AT381837B/de not_active IP Right Cessation
- 1982-12-02 GR GR69970A patent/GR79557B/el unknown
- 1982-12-02 RO RO109205A patent/RO85812B/ro unknown
- 1982-12-02 PL PL1982239330A patent/PL131542B1/pl unknown
- 1982-12-02 FR FR8220183A patent/FR2517673B1/fr not_active Expired
- 1982-12-02 CA CA000416852A patent/CA1194481A/en not_active Expired
- 1982-12-02 PH PH28216A patent/PH20418A/en unknown
- 1982-12-02 IT IT24575/82A patent/IT1156131B/it active
- 1982-12-03 SE SE8206923A patent/SE453829B/sv not_active IP Right Cessation
- 1982-12-03 BG BG8258800A patent/BG37072A3/xx unknown
- 1982-12-03 CS CS828746A patent/CS230597B2/cs unknown
- 1982-12-03 HU HU823890A patent/HU188821B/hu unknown
- 1982-12-03 ZW ZW256/82A patent/ZW25682A1/xx unknown
- 1982-12-03 DD DD82245543A patent/DD208294A5/de unknown
- 1982-12-03 ZA ZA828916A patent/ZA828916B/xx unknown
- 1982-12-03 DK DK537982A patent/DK537982A/da not_active Application Discontinuation
- 1982-12-03 KR KR8205427A patent/KR880002041B1/ko active
- 1982-12-03 NO NO824071A patent/NO824071L/no unknown
- 1982-12-03 IL IL67403A patent/IL67403A/xx unknown
- 1982-12-06 US US06/447,624 patent/US4517367A/en not_active Expired - Fee Related
Also Published As
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